title: First synthesis of saponarin, 6-C- and 7-O-di-β-D-glucosylapigenin.
abstract: Saponarin, apigenin 6-C- and 7-O-bis-β-D-glucoside, was synthesized in an overall yield of 37% via 11 steps, which included the C-glycosylation of 2,4-O-dibenzylphloroacetophenone, the introduction of a cinnamoyl residue by aldol condensation, the formation of a flavone by regioselective deprotection, and oxidative ring-closure to the final regioselective deprotection and stereoselective O-glycosylation.
authors.affiliation: Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata 992–8510, Japan.
authors.forename: Kazufumi
authors.initials: K
authors.lastname: Misawa
authors.forename: Yasuko
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Shingo
authors.initials: S
authors.lastname: Sato
mesh_terms: D047310:Apigenin / Q000138:chemical synthesis / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D005960:Glucosides; C457771:saponarin; D047310:Apigenin